Hydrochloric Acid → 2-(2,2,3,3,3-Pentafluoropropyl)malononitrile

HRID 1443606Notes

Reaction equation

HRID 1443606 reaction equation
FC(F)(F)S(O[CH2:7][C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])(=O)=O.[C:17](#[N:21])[CH2:18][C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+].Cl>COCCOC>[F:13][C:8]([F:14])([C:9]([F:12])([F:11])[F:10])[CH2:7][CH:18]([C:17]#[N:21])[C:19]#[N:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 27760192,2,3,3,3-Pentafluoropropyl trifluoromethanesulfonate

Product 1

HCID 866125702-(2,2,3,3,3-Pentafluoropropyl)malononitrileYield 35.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In 30 ml of ethylene glycol dimethyl ether, 8.4 g of 2,2,3,3,3-pentafluoropropyl trifluoromethanesulfonate and 5.9 g of malononitrile were dissolved. Thereto 12.3 g of potassium carbonate was added and the mixture was stirred at room temperature for 8 hours. Thereafter dilute hydrochloric acid was added to the reaction mixture and the mixture was extracted with t-butyl methyl ether. The organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.1 g of 2-(2,2,3,3,3-pentafluoropropyl)malononitrile.

Workup

  1. extractionthe mixture was extracted with t-butyl methyl ether
  2. washThe organic layer was washed successively with water, aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2071d79efa3e4f7392459287c6cfe3b9
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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